


Havana Gorgeous

by Wayward_and_Worn



Category: Supernatural
Genre: F/M
Language: English
Status: Completed
Published: 2019-11-19
Updated: 2019-11-19
Packaged: 2021-02-13 01:09:06
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,530
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21485845
Author URL: https://archiveofourown.org/users/Wayward_and_Worn/pseuds/Wayward_and_Worn
Summary: The reader and the Winchesters find themselves on a sudden vacation in Havana.  And Sam knows just how he wants to spend it.
Relationships: Sam & Reader, Sam & You, Sam Winchester/You, sam winchester & reader, sam winchester x reader
Comments: 4
Kudos: 29





	Havana Gorgeous

**Author's Note:**

> This spawned from Gen’s Instagram when the Padaleckis traveled to Cuba. There is a picture of Jared with a cigar in his mouth. This is my single favorite picture of him to date. His eyes are the most relaxed and content that I’ve ever seen and I just got lost in it.

The music in the background was fading behind the content buzzing in her own body. It had been a long, hard run for the Winchesters and when Dean had burst into the room babbling about a free vacation, Sam and Y/N had worried that he was possessed. Again. 

“Cuba?” Sam had asked incredulously, looking at the pamphlet Dean had thrown down on the table in front of him. “The owner wants to send us to Cuba? As a-a thank-you?”

“It’s Koo-ba.” Dean corrected proudly. “We did just gank a whole nest of vamps for the guy. He told me that he owns this hotel with his brothers, all we have to do is say the word.” He made a sweeping gesture with his arms. “Just a short boat ride and we’re in the land of beautiful cars, beautiful women, and rum!”

“And cigars,” Y/N chimed in.

Dean swung his head towards her, his jade green eyes wide with excitement, “That too!” Turning more serious, he plunked down in the chair next to his brother. “Let’s go. Hell, we’re already in Florida, we’re damn near there! Let’s just go. We could really use the break. You look like hell.”

“Oh, thank you,” Sam retorted, his hazel eyes scanning the pages. There had to be a catch. 

Dean shook his head and huffed, “You know what I mean. You look like hell. I look like hell…Y/N…” He trailed off as he turned towards Y/N, Sam following his brother’s gaze. 

“I look like hell,” she agreed with a smile and nod. She was easing herself off the bed to join the brothers at the table. Sam handed her the pamphlet as she approached and took her place in his lap. 

“And that _beard_, man,” Dean began, turning his attention back to his brother.

“Dean I told you,” Sam sighed into his reply.

“I like the beard,” she defended, reaching out to place her palm against the younger Winchester’s cheek. Dean made an exaggerated gagging face when Sam leaned into her touch. “Shut up, Dean.” 

“Bias.” The elder Winchester blurted. “You said so yourself last night. We are beyond burned out. And you’re right. Please Sammy…Please?” He turned towards Y/N who was now thumbing through the pamphlet. “What do you think?”

“It does look beautiful,” she offered, “But what about—“

“Fuck it,” Sam piped up; earning raised eyebrows from Y/N and a gleeful whoop from Dean. “Let’s go.”

The trip was relatively painless considering their passports were made at Kinko’s. There was a moment of panic when Dean realized that the Impala would NOT be making the journey. However, Ed, the ever so grateful owner, offered his own secure garage to store her. After inspecting the grounds, Dean deemed it worthy and parked Baby away. 

A small army greeted them when the boat docked. Ed had apparently told his family to pull out all the stops. Dean was presented with a giant bottle of rum. One of the big ass glass jugs with a handle. Sam, a box of cigars and a smaller bottle. Y/N was presented with a large shopping bag stuffed full of…something. And, yes, a bottle of rum. At that point, Y/N became a little overwhelmed at the attention. Sam squeezed her hand and pulled her closer to his side as they were herded into a classic, 1957 Chevy and taken to the hotel. 

One of the younger sisters, maybe it was a sister, Y/N wasn’t entirely sure, set her sights on Sam as soon as they entered the lobby. As she was working to get their rooms, she eagerly offered three separates. Sam smiled and shook his head, indicating two. She looked disappointed, but when he raised their entwined hands and kissed Y/N’s knuckles, “Mi Corazon.” Pretty much ended that. 

“Suerte,” she’d replied with another smile, all disappointment vanishing. 

As they headed to their room, Y/N piped up. “What did she call me?” 

Sam smiled at her, leaning down to steal a kiss before they entered their room. “Lucky.” His tired eyes met hers, “Although I think she might have gotten it backwards. I think I’m the lucky one.”

The comforting buzz of her drifting thoughts was disturbed when she felt that she was being watched. Looking up, Sam’s attention was glued to her with the most adoring, content eyes she’d ever seen on him. He was likely high and drunk, but he was beautiful. Her blood heated under his gaze. He raised a cigar to his mouth, and it was the sexiest thing on earth. She licked her lips. 

His gaze didn’t waver, simply watching her while he dragged on the cigar, letting the thick smoke curl lazily from his perfect lips. 

“See something you like?” She finally asked.

He nodded slowly, “You know I do. Every inch.”

She felt exposed in her current attire. In her shopping bag welcome gift, she’d discovered an amazing and beautiful dress, very appropriate for the environment. But completely out of Y/N’s comfort zone. It was off-the-shoulder and form fitting; white with a ruffled pattern of large pink roses and dark forest green leaves. The skirt landed mid-thigh and puffed out just a bit to accent her legs in the tan sandals that had also been provided. She didn’t spend a lot of time trying to figure out how these people managed to know her size. When she saw herself in the mirror, she was almost giddy at the sight of the woman looking back at her. She was damn sexy. And when she stepped out of their bedroom, Sam looked up from where he was on the couch, he damn near swallowed his tongue.

“Do we have to go out?” he’d whined.

Conversation flared back up and Y/N had excused herself to get one more from the bar. Upon returning, she saw that Dean and the sister from earlier were in her spot. With a shrug, she tucked in next to Sam who immediately threw an arm around her, pulling her against his side and resting his hand on her hip. 

She leaned in happy and content. Then, maybe it was the alcohol, maybe it was just the existence of Sam Winchester; a slight tingling in her core sent her lips up to his ear, “I want you.”

His fingertips dug into her side, otherwise, there was no indication that he’d heard. Watching the others, she gripped his hand, moving it to the bare skin of her thigh and up, under her skirt, to the skin of her hip. 

“And then w--…” Sam stuttered, his hand clenching in an almost bruising grip. He recovered quickly to finish with, “We found ourselves in paradise.” He looked down at her, his eyes reflecting the storm in their hazel depths, “Right?”

She nodded innocently, “Absolute paradise.” Sam slipped his hand down taking a generous handful of her ass and squeezing. “You need something?”

“Mmmhmm,” he drawled, leaning in for a kiss, pushing her back against the back of the booth, her hands automatically winding in his hair. Sighing against her lips, “You. Now.”

They bade their companions a hasty farewell as they walked hand in hand to the elevators. While they waited, Sam moved behind her, his hands on her shoulders. His heat radiating all the way to the bottom of her feet. He slid his arms around her, pulling her against his frame. “I’ve been thinking of all the things I want to do to you on that balcony.”

She knew that he felt her tremble, “Like what?”

Her only answer was a hum and his lips on her neck. 

Once in the room, Sam pressed her gently against the door, stealing her breath with his kisses. “Go to the balcony. Sit in one of the chairs.” He grabbed her wrist when she moved to unzip her dress. “Please, leave that on.”

“Really?” The adoration and hunger she found in his eyes only made her hungrier for him. 

He nodded, “I can’t begin to tell you how beautiful you are. And in this,” he ran his fingers down the skirt, “I can’t even breathe.”

She floated to the patio doors, throwing them open to the warm Havana night. Sitting on their patio were two high-backed wicker chairs with a small table between them. The balcony was surrounded by intricate wrought iron. With a contented sigh, she settled into one of the chairs, leaned back, and closed her eyes to soak in the warmth. She was almost dozing in thought until she heard the soft padding of footsteps and then the chill of something solid touching between her knees then pushing up between her thighs. 

Opening her eyes, she was treated to the magnificent sight of Sam Winchester, shirtless, barefoot, and dressed only in cream colored drawstring linen pants. He was offering a beer with an adoring smile. “You look so gorgeous like this.” He stepped back, taking his own seat on the other side of the small table. 

“Like what?” she questioned. 

“On vacation.”

“You wear relaxation pretty well yourself, buster.” She tipped the bottle to her lips, acutely aware of Sam watching her mouth. “You can dress like that more often.” 

They sat in comfortable silence, working on their beer as the night cooled slightly around them. When her mind stopped drifting and returned to the present, she felt his eyes back on her. She turned to see him, head resting on the back of his chair, half-open eyes focused on her. A slight grin on his handsome face.

“Sleepy?” She asked with a grin.

He shook his head. “Hungry.” Before she could follow up, he sat up, eyes more alert. “Pull up your dress a little,” he said. 

She shivered at his command. Even seated, the skirt rested higher on her thighs. Tilting her head, she slowly ran her hands down to her knees, then up, pushing the fabric higher as he watched. Closely. She held his eyes as she let her legs part a bit, leaning over to put her empty bottle on the table. “How long are you gonna stay over there?”

A breathy laugh as he slapped his hands down on his legs and pushed to standing. Closing the space and dropping to his knees before her he leaned in for a kiss. He pushed his body between her legs and pulled her against him. His beard was rough against her cheeks and she adored the friction. 

“I love you,” he murmured against her neck, “I love you so much.”

Running her hands through his long hair, “Sam…baby…” he kissed her again, his tongue cutting off any more words as it swirled with hers. When she finally could speak again, she continued, “Love you.”

He held her close, “You feel so good. God, it’s so great to be alone with you. No monsters. No research. No…fucking DEAN.” He laughed. “Just me, and my girl.” 

It wasn’t long before his large hands were pushing her dress higher around her waist. Smoothing over her bare hips and he licked his lips like a predator. “Hungry.” He slid her to the end of the chair and leaned in quickly, parting her folds with his fingers and slipping his tongue inside. His beard was rough on her inner thighs, only adding to the pleasure. Her hips immediately moved with him. 

She didn’t even register his movements, gasping his name at the intrusion of his fingers. Coupled with his tongue, she was shuddering. He responded with a growl, leaning forward, pushing his shoulders under her thighs, her legs now over his body. He bore down, focusing harder on her clit, pushing in with his fingers. Pleasure rocked her nerves. 

“Oh God, Sam,” she whined.

Pulling back, he stood, he tugged quickly at the drawstring and let his pants drop to pool around his feet. She leaned in, taking him into her mouth. He cried her name while wrapping a hand in her hair, guiding her along his length. 

She wrapped a hand beneath his sack, cradling him, this time it was his turn to shudder. “You’re so perfect…” he began, “so good…” he moaned, “How did I get so lucky…to…unnnh…oh god…” his babbling only adding to her desire to please him. “Nnnh! Y/N…” he pulled gently on her hair, tugging her back. When her eyes met his he spoke, “Get on those rails. I want to fuck you from behind, facing Havana. I want you to scream my name from this balcony when you come.”

She slowed her movements, feeling him drag within her walls. The vision of what he wanted making her want him even more. She stood and made her way to the center of the balcony. The city was a golden glow beneath them. Sounds of the nightlife wafted up to their ears. She could see people milling around in the street below. They were only six floors up. She stepped up on a cross bar, making her a better height for him. As she positioned, her dress fell back into place. Expecting large hands to yank the material back up, she was startled when he pressed against her back instead. He wrapped one arm around her shoulders, the other around her waist. 

He stood still, his chin on her shoulder, gazing out at the landscape with her. 

She could feel him, still hard, pressed against her backside. She began to sway her hips back and forth against him. 

“Feels good,” he purred into her ear. 

Turning her head, she met his lips, pushing her tongue inside to taste him. She arched her back, using the leverage to kiss him harder. She then ran her hands down to the bottom of her dress and slowly slid the fabric back up around her waist. His cock, now pressed hot against her, twitched in need.

“Open your legs.”

She stepped over, parting her thighs as commanded. Gripping the rail tightly, she hissed in pleasure as he sheathed himself within her again. He placed his hands next to hers at the railing and began moving in and out.

He rocked her at a slow pace for so long, her legs started to burn from holding her balance. “Sam,” she whined, pushing back against him.

“Do you wanna come?” he panted in her ear. She could feel the sweat on his skin as he pushed against her. Before she could reply, he pulled back, leaving her empty. “Let’s get this off before I destroy it.” Deft fingers pulled the zipper at her back, peeling the dress from her body. The air, almost chilly when it hit her bare skin. 

Immediately, his large body was back against her, hoisting her up on the bar, impaling her with a growl. His hands covering her breasts, squeezing hard, just like she liked. “I love you so much.”

A rush of warmth began in her core as Sam started pounding into her. When she reached a hand down to begin massaging her clit, she finally did what he asked. She screamed his name into the Havana night. 


End file.
